(2-Methoxypyridin-4-yl)boronic acid → HCID 60197875, compound

HRID 1631777Notes

Reaction equation

HRID 1631777 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B(O)O)[CH:6]=[CH:5][N:4]=1.Cl[C:13]1[N:22]=[CH:21][C:20]2[NH:19][CH2:18][CH:17]3[CH2:23][O:24][CH2:25][CH2:26][N:16]3[C:15]=2[N:14]=1>O1CCOCC1.C([O-])(O)=O.[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:13]2[N:22]=[CH:21][C:20]3[NH:19][CH2:18][CH:17]4[CH2:23][O:24][CH2:25][CH2:26][N:16]4[C:15]=3[N:14]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 2

HCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 86670087HCID 86670087, compound

Product 1

HCID 60197875HCID 60197875, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using 2-methoxypyridin-4-ylboronic acid (270 mg, 1.765 mmol), 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 200 mg, 0.882 mmol), and PdCl2(dppf) (51.7 mg, 0.071 mmol) in dioxane (5 mL) and aqueous saturated NaHCO3 (1 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.01-3.23 (m, 7H), 3.89 (m, 3H), 3.92-3.97 (m, 1H), 3.99-4.06 (m, 1H), 4.53-4.62 (m, 1H), 7.47 (d, J=0.76 Hz, 1H), 7.62 (s, 1H), 7.68 (dd, J=5.31, 1.52 Hz, 1H), 8.24 (d, J=5.56 Hz, 1H). ESI-MS m/z [M+H]+ calc'd for C15H17N5O2, 299.14. found 300.2.

Sources & evidence

ORD record
ord-660424de10904cac8985387a1051aed1
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

Loading…